2-Aminopyrimidine → Methyl 2-[[[(2-pyrimidinylamino)carbonyl]amino]sulfonyl]benzoate

HRID 280801Notes

Reaction equation

HRID 280801 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19])=[O:11]>C(#N)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[NH:1][C:22]([NH:21][S:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]([O:9][CH3:8])=[O:11])(=[O:20])=[O:19])=[O:23]

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 13176579Methyl 2-[[[(2-pyrimidinylamino)carbonyl]amino]sulfonyl]benzoateYield 65.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

With stirring at ambient temperature, 1.0 g of 2-aminopyrimidine in 25 ml of anhydrous acetonitrile was added to 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring that mixture for 24 hours, the resultant precipitate was filtered off to yield 2.2 g of the desired compound which melted at 188°-192°. Its showing infrared absorption peaks at 1700, 1680 and 1580 cm-1 is consistent for N-[(pyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide.

Workup

  1. stirringAfter stirring that mixture for 24 hours
  2. filtrationthe resultant precipitate was filtered off

Sources & evidence

ORD record
ord-13344968fec14654aa02bdc6371a1113
Source dataset
uspto-grants-1986_05
Patent number
US04591378

Reaction notes

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